Hydroxylamine, H2NOH, has both an OH functional group and an NH2 functional group, so it can feasibly undergo reaction with a ketone or an aldehyde to produce either an acetal or an imine-like compound called an oxime. (a) Draw each of these mechanisms for the reaction of hydroxylamine with acetone. (b) Which is the major product? Hint: Which step decides the outcome?

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.82P: The following molecule undergoes an intramolecular reaction in the presence of pyrrolidinium...
icon
Related questions
icon
Concept explainers
Question

Hydroxylamine, H2NOH, has both an OH functional group and an NH2 functional group, so it can feasibly undergo reaction with a ketone or an aldehyde to produce either an acetal or an imine-like compound called an oxime. (a) Draw each of these mechanisms for the reaction of hydroxylamine with acetone. (b) Which is the major product? Hint: Which step decides the outcome?

Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Catalysis and Enzymatic Reactions
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
Recommended textbooks for you
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning